You've seen all the tutorials and getting-started guides promising a quick path to a web API: pick between REST or GraphQL, choose an API framework, and deploy it to the cloud. But what happens when you need to modify, expand, share, or overhaul that API once it is already live in production? In this talk, we’ll explore the real-world challenges we faced as our web APIs evolved over several years. We’ll discuss how initial decisions and insufficient planning led us into pitfalls, resulting in tech debt and obstacles when it came time to evolve our APIs. By addressing design concerns like a well-documented API specification, versioning, Infrastructure as Code (IaC), an API gateway, and enhanced observability, we can avoid future rework and minimize disruption for our customers. Join us to learn strategies for navigating the complexities of evolving APIs and ensuring a smoother path from inception to long-term success.